Gloucester Garden Tours
Generous Gardener’s primary annual fundraiser is our Gloucester Garden Tour. This event began in 2013 to raise funds for flowers at the Fishermen’s Wives Memorial. Each year’s tour is held in a different part of Gloucester, where generous garden owners open their private spaces to the public for one day to benefit all of the public gardens in Gloucester.
2026: Eastern Shore of Gloucester
Tickets are on sale now for our 2026 Tour, to be held on Saturday, July 11th, 2026, from 9:30 AM to 3:00 PM on the scenic, coastal, and historic eastern shore of Gloucester.
Get more information and purchase tickets.
Tour the scenic, coastal, and historic eastern shore of Gloucester, a popular summer destination for affluent Boston families in the late 19th and early 20th centuries. Many of the grand homes from that era with equally beautiful gardens still stand, and several are included on our tour. Each owner approaches gardening differently, so you will be treated to a range of formal designs to cottage gardens, and an amazing garden that is a garden tour in itself. There is a tea house, a classic orchid greenhouse, and spectacular ocean views.
2025: Magnolia Seaside
This year’s Generous Gardeners tour was in the Magnolia neighborhood in Gloucester. Magnolia is storybook beautiful, with its stunning ocean views along Shore Road and a welcoming community. The gardens are a delightful mix of styles and sizes and includes an amazing historic Olmsted garden. Once home to grand summer hotels, this storied enclave is now filled with beautiful homes, stunning waterfront scenery, and flourishing gardens.
2024: Wheeler’s Point
This unique neighborhood, surrounded by the Annisquam River, the Mill River, Ipswich Bay and Jones Creek, presented several gardens with stunning water views. The gardeners themselves ranged from novice to very experienced and provided a full range of annual, perennial and vegetable gardens.
2023: Downtown Gloucester
Our 11th Annual Gloucester Garden Tour commemorated Gloucester’s 400th anniversary with a tour of greater downtown neighborhoods. The tour took you along historic streets and by the famous Fisherman’s Memorial on Stacy Boulevard designed one hundred years ago for the 300th anniversary of the city. Gloucester is a vibrant city of diverse neighborhoods, with a variety of urban gardens, from small front yards to hidden back gardens. Some are attached to historic homes, one has an amazing hilltop harbor view, and another is a botanical delight. All the gardens are the work of their owners, and they are certain to inspire you with their originality.
2022: West Gloucester
The 10th annual Generous Gardeners Garden Tour was in West Gloucester. Despite being established as “Second Parish” or “West Parish” by 1718, this area continued to be the most sparsely settled of all Gloucester’s neighborhoods. The Annisquam River separates it from the island of Gloucester and it is now, as it was then, a land of deep woods and marshes. The gardens are located along winding, narrow roads that cut through the woods where bridges cross sections of the Great Marsh. Most of the gardens are gardener’s gardens, designed and built by the owners, while one is the creation of a world class professional garden designer. Some are small and intimate but a few are extensive, Some have stunning views of the marsh while others tame a little of the woods, and one is actually in the woods.
2021: East Gloucester
The 9th annual garden tour is an exploration of fourteen gorgeous gardens in the Mount Pleasant Avenue area of East Gloucester. Most of the gardens you will see today are “gardeners’ gardens” designed, planted, and maintained by their owners. There are stunning views from many of the gardens which overlook the working harbor and the center of the city. The architecture of many of the homes and building along the route is notable, including the beautifully restored 1873 fire barn at the corner of Mount Pleasant Avenue and Chapel Street.
2020: Virtual Tour
The 8th annual garden tour was a virtual tour of our volunteers gardens as no in person events were allowed due to Covid 19.
The online video available was a wonderful break and volunteers videoed their gardens or sent photos for slide shows set to music.
2019: Bass Rocks / Back Shore near Good Harbor Beach
Traveling along the Back Shore is to experience the grandeur of the Atlantic Ocean in its full glory. The magnificent vistas include Good Harbor Beach, the twin lighthouses on Thacher Island, and the waves crashing along miles of rocky shore. When French explorer Samuel de Champlain visited the area in 1606 he named it Le Beau Port meaning the beautiful harbor, and on this tour, you will easily understand why.
This year’s Generous Gardeners’ Garden Tour will provide the opportunity to see hidden backyard gardens behind many of the impressive facades on Atlantic Road and neighboring roads. Explore gorgeous private gardens along Gloucester’s stunning Back Shore.
2018: Lanesville
The sixth annual Gloucester Garden Tour was in the intriguing Lanesville neighborhood. Over 600 visitors explored more than a dozen lovely private gardens, quarries and enjoyed the gorgeous ocean views. Originally accessible only by stagecoach, Lanesville is the northern-most neighborhood of Gloucester. In the 1800’s Lanesville granite was quarried, cut and shipped from Lanes Cove via “granite sloops” to pave roads in New York, Philadelphia and Boston. Even the stone overpasses of Route 128 were constructed with Lanesville granite in the 1950’s. The granite industry was active in the area for over one hundred years. Scenes from the granite quarrying business and related themes appear in artwork created by artists who discovered the neighborhood. Paul Manship and Walker Hancock both built their studios on abandoned quarries in the 20th century. Virginia Lee Burton established her famous Folly Cove Designers and wrote children’s books still beloved today, including Mike Mulligan and His Steam Shovel. Today, Lanesville continues to inspire artists and authors.
2017: The Village of Magnolia
The fifth annual Gloucester Garden Tour was in the historic neighborhood of Magnolia. Attendees toured 14 impressive gardens, including one designed by the famous Olmsted firm. The village of Magnolia straddles the border of Gloucester and Manchester-By-The-Sea. In its heyday, Magnolia was a fashionable destination for the wealthy to summer. The huge Oceanside Hotel and the smaller Magnolia Manor drew the rich and famous to the village. There were posh stores like Tiffany’s lining Lexington Avenue and mansions along Shore Road. Today Magnolia is a quiet residential neighborhood but it still retains remnants of grander days. This tour was a a varied mix of cottage gardens, rose gardens and estate gardens with fabulous ocean views as you strolled along Shore Road.
2016: Eastern Point Enclave
Gloucester is a city of neighborhoods and Eastern Point is undeniably the most exclusive of all. Eastern Point has been settled since at least 1728, but it was after 1887 that it became a vacation spot for the wealthy who built magnificent “cottages.” This neighborhood is so exclusive that a State Supreme Court ruling in 1859 actually affirmed the right to bar the public from entering Eastern Point. Fortunately, visitors were allowed to pass through the stone gates and view 11 incredible estate gardens. In addition, Historic New England opened the gardens of Beauport, the historic home built by Henry Sleeper from 1907 to 1934
2015: Annisquam Village
in 2015 Generous Gardeners presented a walking tour of 15 gardens in the Annisquam village neighborhood of Gloucester. The village of Annisquam was first settled in 1656. Annisquam is said to be an Indian name, “squam” being the Indian word for harbor, but the early settlers found no evidence of natives. They developed the village for shipbuilding and eventually for trade. Much later it became popular as a summer resort. Many of the houses in the village are historic and the architecture is quintessential New England. Vehicular traffic is very limited by a single entry road into the village. A drawbridge, built in 1847 over Lobster Cove, once served carriages but it was replaced in the late 1980’s by the current pedestrian-only footbridge. The footbridge is a rare example of a wood pile and timber stringer bridge and is listed on the National Register of Historic Places.
2014: Gloucester’s Back Shore
The second Generous Gardeners tour included 12 fabulous gardens located along the Back Shore of Gloucester. Some of the gardens were expansive, others were intimate, and many had breathtaking ocean views. In addition, one of the gardens featured a unique “man cave” and another garden included a classic car collection.
2013: WEST GLOUCESTER AT BISKIE HEAD POINT, HOLDSWORTH GARDENS AND THE OLD STACY BOULEVARD GARDENS
Generous Gardeners held their first garden tour in West Gloucester. Hillary Holdsworth opened her wonderful gardens, and Susan Kelly and other Biskie Head Neighbors were also on this tour. Generous Gardeners also included the (then) small Stacy Boulevard Gardens.
